2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

Base Information

Chemical Name:2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine
CAS No.:733050-18-5
Molecular Formula:C₃₀H₃₉Cl₂N₃O₅Si
Molecular Weight:620.648
Hs Code.:

Synonyms:2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

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Chemical Property of 2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

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Technology Process of 2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

There total 7 articles about 2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 733050-17-4
3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-2'-α-hydroxymethylcytidine

: 733050-18-5
2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

Guidance literature:: With pyridine; at 20 ℃; for 24h;
DOI:10.1021/jo0495337

Reference yield:

: 108008-66-8
methyl 3,5-di-O-(4-chlorobenzyl)-α-D-ribofuranoside

: 733050-18-5
2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.1: s-BuLi / cyclohexane; tetrahydrofuran / 1 h / -78 °C

2.2: 63 percent / cyclohexane; tetrahydrofuran / -78 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

3.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

4.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

5.1: TMS₂NH; (NH₄)2SO₄ / 1 h / Heating

5.2: 55 percent / SnCl₄ / acetonitrile / 20 - 60 °C

6.1: 83 percent / NH₃ / methanol / 48 h / 0 - 4 °C

7.1: 93 percent / pyridine / 24 h / 20 °C

With pyridine; dmap; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; sec.-butyllithium; Dess-Martin periodane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; 1.1: Dess-Martin oxidation;
DOI:10.1021/jo0495337

Reference yield:

: 733050-11-8
methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside

: 733050-18-5
2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: s-BuLi / cyclohexane; tetrahydrofuran / 1 h / -78 °C

1.2: 63 percent / cyclohexane; tetrahydrofuran / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

2.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

3.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

4.1: TMS₂NH; (NH₄)2SO₄ / 1 h / Heating

4.2: 55 percent / SnCl₄ / acetonitrile / 20 - 60 °C

5.1: 83 percent / NH₃ / methanol / 48 h / 0 - 4 °C

6.1: 93 percent / pyridine / 24 h / 20 °C

With pyridine; dmap; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; sec.-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; cyclohexane;
DOI:10.1021/jo0495337